Journal of the American Chemical Society

Effective route to azetidines from azetidin-2-ones with the use of hydroalanes as specific reducing agents

M Yamashita, I Ojima

Index: Yamashita, Mitsuo; Ojima, Iwao Journal of the American Chemical Society, 1983 , vol. 105, # 20 p. 6339 - 6342

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Citation Number: 46

Abstract

We chose 3-benzyloxy-1, 4-diphenylazetidin-2-0ne (la) as a typical substrate and examined various metal hydride reducing agents. Attempted reduction by BH3. THF (22 h in refluxing dioxane) and NaBH,-AlC1,(3.5 h in refluxing ether) resulted in the complete recovery of the starting substrate and the reduction with LiAlH,, LiBEt, H, or LiB-sec-Bu3H gave 3-(phenyl- amino)-3-phenyl-2-(benzyloxy) propanol (3a) exclusively through